p-Cymenesulphonyl Chloride: A Bio-Based Activating Group and Protecting Group for Greener Organic Synthesis

A bio-derived protecting/activating group has been synthesized by introducing a sulphonyl chloride group to the aromatic ring of p-cymene derived from citrus peel waste. The resulting p-cymenesulphonyl chloride was evaluated as an activating group by reacting with 1-octanol, 2-octanol, phenol and piperidine, and further reactions of the activated alcohols. The comparison to tosyl chloride demonstrates that the bio-based alternative can be effectively utilized as a direct replacement for the current fossil derived equivalent.

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Bibliographic Details
Main Authors: Farmer,Thomas J., Clark,James H., Gothe,Maite L., Macquarrie,Duncan J., Sherwood,James
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2015
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015000901914
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Description
Summary:A bio-derived protecting/activating group has been synthesized by introducing a sulphonyl chloride group to the aromatic ring of p-cymene derived from citrus peel waste. The resulting p-cymenesulphonyl chloride was evaluated as an activating group by reacting with 1-octanol, 2-octanol, phenol and piperidine, and further reactions of the activated alcohols. The comparison to tosyl chloride demonstrates that the bio-based alternative can be effectively utilized as a direct replacement for the current fossil derived equivalent.